Product School

How to Excel as a Digital Transformation Leader: Choosing the Right Talent

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Carlos González De Villaumbrosia

October 31, 2023 - 9 min read

Updated: May 6, 2024 - 9 min read

Companies across diverse sectors, whether it's healthcare, manufacturing, or finance, are eagerly diving into digital transformation. The appeal of "Big Data", user-friendly interfaces, and instantaneous services is real. The key to it all— being an outstanding digital transformation leader.

Digital Transformation isn’t just about cutting-edge technology, but the visionaries leading it. This article unpacks the vital balance between 'digital natives' and 'digital immigrants' and why both are critical for a company's digital journey.  With insights into internal talent development, traits of digital leadership, and the hunt for external digital expertise, the piece goes beyond the tech to explore the human side of transformation.

Want to find out the secrets to attracting, onboarding, and retaining the best digital talent? Read on and uncover the best strategies to blend the talent you need.

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The digital spectrum

Nowadays, digital transformation leaders have to face fascinating dilemmas. You have your 'digital natives' – those for whom digital technologies have been a given since their formative years; and the 'digital immigrants', the stalwarts who have adapted to the digital world, combining their experience with newfound digital aptitude.

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Depth vs. Breadth

Let’s have a look at what makes each standout:

Digital Natives

Their innate comfort with technology sets them apart. With an inclination to delve deep into their specializations, they seek mastery in particular niches. Driven by precision and structure, their roles are often well-defined, with clarity and an eye for detail being their forte. 

For instance,  consider Brian Chesky, the co-founder and CEO of Airbnb. He can be identified as a digital native since he has been instrumental in reshaping the hospitality industry through a digital lens. His approach to digital product development embodies the essence of digital natives.

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Chesky's leadership at Airbnb, his focus on iterative digital product improvements based on user feedback, and his commitment to creating an intuitive online user experience showcase the mindset and skillset of a digital native in product.

Digital Immigrants

These are expert-level professionals, those who've gone through the traditional path. Their advantage? Vast experience. Their transitioning into the digital scene gives them a combined set of skills. 

They master the different degrees of influence – an essential asset when leading change in big corporations. Their ability to discern connections, bridge gaps, and leverage their empathetic skills makes them indispensable, especially when threading digital strategies into legacy systems.

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A prime example of a digital immigrant in the tech industry is Satya Nadella, the CEO of Microsoft. Nadella did not grow up immersed in the digital technologies that characterize the lives of digital natives. However, during his professional career, he successfully transitioned into the digital era.

Under his leadership, Microsoft underwent a significant transformation, shifting focus to cloud computing with Azure and adopting a more open-source and collaborative approach, as seen with Microsoft's acquisition of GitHub and its embrace of Linux. 

So, both skill sets bring irreplaceable value to the table when going through digital transformation. There's room for the specialist's depth just as there's a need for the generalist's breadth. The key lies in discerning when to delve deep and when to encompass a broader perspective.

Traits and competencies of digital leadership

To truly excel in guiding digital transformations, there are qualities, skills, and motivations you must hone. 

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Let's have a look into the contrasts and commonalities that define leaders from 'born-digital' backgrounds and those transitioning into the digital scenario.

1. Defining traits of digital leaders

Cultural dexterity: More than just cultural awareness, it's the synergy of cultural knowledge, emotional intelligence, and interpersonal skills. It's about thriving, not just surviving, in any cross-cultural scenario.

Learning agility: A hallmark of great leaders, this is the aptitude to extrapolate lessons from past experiences and adeptly apply them to novel scenarios.

Emotional intelligence: It's the intuitive ability to resonate with, comprehend, and respond to the emotional responses of others.

2. Core competencies 

Thought: This involves a deep business acumen, the mental bandwidth to make complex decisions, and the ability to innovate and transform.

Results: Focused on proactive initiation, strong execution, and a laser focus on performance metrics.

People: An emblem of leadership, it revolves around nurturing collaborative relationships, leveraging diverse talent pools, and wielding influence effectively.

Self: Authentic existence paired with the flexibility to adapt and the openness to embrace the unknown.

In short, born-digital executives value autonomy and flexibility, excelling in rapid learning and often preferring to work independently. Meanwhile, going-digital leaders excel in relationship-building, teamwork, and communication. They're adept at handling challenges and rallying teams.  Then, for a thriving organizational digital transformation success, both skill sets are non-negotiable. 

Fostering  digital transformation from within

Take a moment and peer into your organization. Nestled within, regardless of the company's age or size, are individuals with digital potential. Some have mastered the digital code, others are eager to ride the digital wave, and a few are just awaiting the nudge to leap into the digital deep end. This mix of readiness forms a wide scenario of opportunity and challenge.

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On top of it, leaders ready for the digital age stand out. They possess a thirst for experimentation, thriving in dynamic atmospheres where rapid testing, immediate feedback, and the thrill of iteration are everyday norms. It's not just about adapting to new situations for them—it's about drawing from past experiences, extracting invaluable insights, and ingeniously applying them to novel situations.

The current strategy? Adopt a dual-track approach. First, pinpoint and promote individuals ready to become digital transformation leaders to enhance immediate digital transformation efforts. Next, focus on expanding overall digital skills. As a result, the entire organization's ability to transform will strengthen.


Being digitally primed isn't just about ticking off a list of skills; it's embodying a blend of adaptability and innovation skills. Here's what this entails:

Mental agility

A mind that thrives on critical thought, delves into complexities, identifies emerging patterns, and then crafts these insights into understandable narratives. This ability to combine complex insights with clear communication is a signature strength.

Change agility

More profound than mere adaptability, change agility entails a hunger for new ideas, an ongoing quest for growth, and an unyielding resilience amidst change.

So, recognizing where your internal talent shines and where it might need improvement is pivotal. This insight not only sharpens immediate strategies but also illuminates the path for your next transformative steps.

The hunt for external digital expertise

Your internal talent is undeniably a goldmine. Yet, there are moments when broadening the horizon, and looking externally, becomes key to elevate your digital stature.

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It's tempting to believe that every digital expert from giants like Amazon or Google is the missing puzzle piece in your transformation journey. However, keep in mind that many of these experts, accustomed to simpler and self-governing environments, may struggle to handle the complexities of traditional corporate settings.

It's all about alignment, so ensure that the digital expert you eye complements the cultural fibers, regional intricacies, and core values of your organization.

What’s the best strategy to attract, onboard, and retain the right talent for your organization?

Currently, there's a notable rise in emerging digital experts. While their skills are top-notch, they might still be shaping their leadership journey. Being digitally savvy is commendable, but true leadership is built on experiences and challenges, which they might still be accumulating.

You've probably heard of "evangelists". They lead companies into the digital age, instilling key practices and mindsets. However, their enthusiasm doesn't always equate to creating strategic business plans, especially in tech hubs like Silicon Valley.

High-caliber digital talent is in demand and they have many options. As these experts expand their capabilities, the available talent pool shrinks. This makes a well-planned talent strategy vital. When recruiting, focus on precision, patience, and ensuring goals align.

1. Crafting an offer digital talent can't overlook

In today's hyper-competitive talent scene, simply identifying top-tier digital talent isn't enough. It's essential to design an offer that resonates with their aspirations and stands out from the crowd.

Offer more than just a salary

Yes, compensation matters. But for the crème de la crème of the digital sector, a lucrative package extends beyond a paycheck. Consider:

  • Compensation creativity: Incentive plans that reflect their impact can be a game-changer.

  • Ownership feel: Offering stock options or RSUs can foster a deeper sense of belonging.

  • Work-life balance: Today's talents expect, if not demand, flexibility – be it in work hours or location.

  • Starting strong: A substantial signing bonus can be the perfect welcome note.

Define your expectations clearly 

Are you in search of a forward-thinking strategist, a technology expert, or a business-savvy professional? While many roles might require a blend of these skills, it's key to pinpoint your primary needs. Moreover, the perfect candidate should naturally align with your company's values and culture.

Showcase your brand beyond products

Your employer brand is equally crucial in this talent chase. The brightest minds often align themselves with companies whose visions resonate with their own. So, spotlight your organization's purpose, mission, and future vision. And yes, this branding is a boardroom-level priority.

But, how do you ensure the digital whizzes, cultivated in cutting-edge environments, adjust to more traditional setups? Traits like adaptability, emotional intelligence, and learning agility are vital. These attributes not only ensure alignment but also avert possible missteps.

2. Solid onboarding: Starting is half the battle

First impressions matter. Especially for digital experts entering a conventional setting. A structured and supportive onboarding ensures they integrate quickly, boosting their contributions and your digital ambitions.

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3. Retaining the digital talent

Retention is the real test. Keeping your digital stars engaged and committed demands foresight and strategy.

Championing your in-house digital stars

Your internal digital talent pool is not only an asset for you but is also eyed by competitors. It's imperative to provide an environment where they feel valued and challenged. To ensure they stay engaged:

  • Continuous Learning: Offer regular training sessions and certifications.

  • Recognition: Timely acknowledgment and rewards boost loyalty.

  • A Culture of Experimentation: Empower them to innovate, ensuring they know failures are stepping stones.

Keeping the digital nomad engaged

Digital experts have an inherent itch for challenges. Once they conquer one, they look for the next. Your role? Make their journey rich and rewarding.

  • Value their time: Recognize their potential transient nature. Let them mentor and influence broader teams.

  • Promote 'digital osmosis': Implement programs to ensure seamless knowledge transfer from these experts to your core teams.

  • Craft unique career arcs: Traditional growth paths might not allure all. Designing dynamic, exciting career paths can keep them engaged longer.

In sum, your journey toward digital excellence is multifaceted. It's about the right hires, the right environment, and the right mindset. Equip yourself and your teams with these, and you're not just preparing for a digital future—you're leading it. 

Updated: May 6, 2024

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